Phorboxazole synthetic studies. 2. Construction of a C(20-28) subtarget, a further extension of the Petasis-Ferrier rearrangement

被引：61

作者：

Smith, AB ^{[1
]}

Minbiole, KP

Verhoest, PR

Beauchamp, TJ

机构：

[1] Univ Penn, Res Struct Matter Lab, Dept Chem, Philadelphia, PA 19104 USA

[2] Univ Penn, Monell Chem Senses Ctr, Philadelphia, PA 19104 USA

来源：

ORGANIC LETTERS | 1999年 / 1卷 / 06期

关键词：

D O I：

10.1021/ol990829m

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHICS] In this, the second of two Letters, we describe the efficient assembly of (+)-4, a C(20-28) subtarget for the total synthesis of phorboxazoles A (1) and B (2), The synthesis was achieved in 12 linear steps (20% overall yield) via Petasis-Ferrier rearrangement of an NZ mixture of trisubstituted enol ethers (15) to assemble the C(22-26) cis-tetrahydropyran. A mechanism for the observed diastereoconvergence of 15 is proposed, In addition, a new tactic for the synthesis of enol ethers (e.g,, 15) based on the elegant work of Julia is described.

引用

页码：913 / 916

页数：4

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